Lithium Chloride → 7-Bromo-2-cyclopropyl-5-methyl-6-vinylbenzo[d]thiazole

HRID 1468692Notes

Reaction equation

HRID 1468692 reaction equation
FC(F)(F)S(O[C:7]1[C:18]([CH3:19])=[CH:17][C:10]2[N:11]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[S:13][C:9]=2[C:8]=1[Br:20])(=O)=O.[CH2:23](C([Sn])=C(CCCC)CCCC)[CH2:24]CC.[Li+].[Cl-]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:20][C:8]1[C:9]2[S:13][C:12]([CH:14]3[CH2:16][CH2:15]3)=[N:11][C:10]=2[CH:17]=[C:18]([CH3:19])[C:7]=1[CH:23]=[CH2:24]

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 53438229Tri(butyl)vinyltinHCID 891582137-Bromo-2-cyclopropyl-5-methylbenzo[d]thiazol-6-yl trifluoromethanesulfonate

Product 1

HCID 891578377-Bromo-2-cyclopropyl-5-methyl-6-vinylbenzo[d]thiazole

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-bromo-2-cyclopropyl-5-methylbenzo[d]thiazol-6-yl trifluoromethanesulfonate (16) (410 mg, 0.988 mmol) in DMF (4 ml), was added tributylvinyltin (0.43 ml, 1.47 mmol), LiCl (125 mg, 2.94 mmol) and PdCl2(PPh3)2 (70 mg, 0.096 mmol). The reaction mixture was reacted at 80° C. overnight. The reaction was cooled down, washed by saturated NaHCO3 solution, extracted by EtOAc. The organic phase was combined, dry over MgSO4, filtered, concentrated and purified by silica gel column, eluting by 0-50% EtOAc in hexanes.

Workup

  1. customThe reaction mixture was reacted at 80° C. overnight
  2. temperatureThe reaction was cooled down
  3. washwashed by saturated NaHCO3 solution
  4. extractionextracted by EtOAc
  5. dry with materialdry over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel column
  9. washeluting by 0-50% EtOAc in hexanes

Sources & evidence

ORD record
ord-a96f2d525dde40f89ae1d5f04ecc9a59
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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